Getting Around Town With Jamie Shupak: Find Yourself, Find a Girlfriend

The other day a guy friend told me that his goal for fall is to find a girlfriend. My first thought: Slow your roll, it’s only August. My second thought: You’ll never find one if you’re trying too hard.

I guess he wasn’t too far ahead of himself though, as Monday is Labor Day, the unofficial end of summer. If you’re ready to transition from warm weather fling to under-the-covers snuggle-buddy, there are a few things you can do to help your cause.

What you need to do is work on yourself.

But first, a word of warning: There are a lot of girls out there who just want a boyfriend. Sometimes, those are the girls to avoid. You don’t want a woman who’s desperate for love and attention. You want a confident one, with plans for this weekend and a future that doesn’t rely on a man.

What you need to do is work on yourself. A personal trainer who reads this column regularly emailed to say that he works with plenty of single men who, once in the habit of taking care of themselves and living a healthier, more physically challenging life, inevitably meet someone. It makes sense. Working out doesn’t just make you more appealing on the outside. Knowing that you’re doing something for yourself, and that you look better in the process, gives you more confidence. More confidence makes it easier to approach the woman you’re interested in.

You should also keep up on your hygiene. Don’t slack because there isn’t a girl in your bed every night. Buy some deodorant, cologne, and aftershave. The last thing a woman wants to smell on a guy is the same scent wafting from her garbage this morning. Get a haircut and make sure you get one regularly. Make sure you also brush and floss regularly, too. Keeping up with this sort of grooming will make you more approachable—and dateable.

It also shows a woman that you value yourself enough to take care of yourself. A woman won’t want to put effort into you if you don’t put in some effort first.

Now that you’re looking good, smelling good, and feeling good, you’ll want to have something interesting to say when you approach. Complimenting her on something she’s wearing, saying, or doing is a great ice-breaker, but you’ll need a strong follow up. That’s why you should also be spending your time reading—an interesting book, a good newspaper, a fun magazine (hi, Complex!). Think of this material as your arsenal. You want to go into a conversation with as much ammunition as possible, so as your target—this beautiful, confident woman—moves around, you can hang with her instead of being struck speechless.

Once she sees how interesting and educated you are, it’s time to apply the full court press. This means answering texts, emails, and calls in a timely fashion. You need to be reliable and easy to communicate with, or she’ll never want to date you. This also means remembering what’s happening in her life, what concerns she has, and reaching out to let her know you’re thinking about her. If she has a big work project, ask how it’s going, or if you can bring her some frozen yogurt while she’s working. If she’s worried about a friend or family member who isn’t doing well, offer to visit that person with her. A woman wants to know you will not only be there for her, but the people she loves, too.

While you’re working your magic, keep going on other dates to remain a bit elusive and to keep your options open. And to keep practicing! But if you’re interested in her, make sure she knows it. Book your next date with her by calling her the next day to say thank you, and that you’d love to do it again. In this land of texting and tweeting, you’d be surprised how far a phone call goes.

You get the point. Act like a boyfriend, and you might just get the job.